The eyeball boss easily, I forgot his name but hes freakin awesome. The battle is tough as shit and the music is awesome, and his animation is done so well you almost forget you're playing a ps2 game.
I'd probably have to say Portal. There are so many lines in that game that made me laugh so hard I forgot what I was supposed to be doing. Especially the final boss, nothing is better than destroying a boss and having it try and demoralize you with increasingly awful insults. Finally, once that crazy robot bitch is melted, out of nowhere, you get the most awesome and random musical experience ever. Classic....
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